


Dean Winchester: Kindergarten Teacher

by deanstrenchcoatangel



Category: Supernatural
Genre: F/F, F/M, M/M
Language: English
Status: In-Progress
Published: 2014-03-09
Updated: 2014-04-06
Packaged: 2018-01-15 02:32:04
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 6,866
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1287970
Author URL: https://archiveofourown.org/users/deanstrenchcoatangel/pseuds/deanstrenchcoatangel
Summary: <blockquote class="userstuff">
              <p>If there was one thing that Dean Winchester loved about teaching kindergarteners, it was their innocence. He loved seeing their hopeful smiles, the wonder that filled their eyes, and their complete and utter faith in humanity. Yes, that was what Dean loved about teaching. That, and the hot new art teacher from two states over. Yeah, that too.</p>
            </blockquote>





	1. First Day Jitters

**Author's Note:**

> I really like this so far! I hope you guys do too! Feel free to leave comments, kudos, and bookmark! (Please) I am rather proud of this and it is fun to write! I want to post daily (if I can) and I will respond to any and all comments! :) Have fun reading!

If there was one thing that Dean Winchester loved about teaching kindergarteners, it was their innocence. He loved seeing their hopeful smiles, the wonder that filled their eyes, and their complete and utter faith in humanity. Yes, that was what Dean loved about teaching. That, and the hot new art teacher from two states over. Yeah, that too. 

It all started that Monday morning, first day back to school. Dean chuckled, leaning back against the wall of the gymnasium, his best friend Charlie going on about a hot girl she had banged the night before. “Man, Dean, have you ever had sex that was so good that afterward, you sat there thinking, ‘holyshitsnacksthatwasgood’? And then you actually consider making it a two-night stand?”

Dean shrugged. “What goes on in the bat cave, stays in the bat cave.”

“So, you had sex with Batman?” Charlie’s eyes grew wide in mock horror. “Why, Dean, you rapscallion!”

He rolled his eyes. “Honey, Batman wishes he could get a piece of this ass.”

Charlie punched him in the arm. “Anyway, like I was saying, this girl had such an amazing body. Like, you could bounce coins off her boobs.” She broke into a fit of laughter. “We may or may not have tried that a few times.”

“Who’s the rapscallion now, eh, Charlie?” Their laughter quickly died out as Naomi, the principal of Kansas Elementary, entered the room. Zachariah, her evil minion, also known as the vice principal, followed in her wake. Chuck, the school’s secretary, cowered beside them. He looked as though he had been drinking, which considering his past incidents, was not an unusual occurrence. 

Once, Chuck had gotten so drunk, that he called an assembly, then used the whole first twenty minutes to ramble on about his ex-girlfriend, Becky. Dean had then tackled him off of the stage, when Chuck had decided to start talking about more intimate details of their relationship. More specifically, their steamy nights together. Chuck had never quite lived that down. 

From the front of the gym, Naomi cleared her throat. “Please, everyone quiet down.” Her voice was gentle, kind, but deceiving. For after a few moments, when a few groups scattered throughout the crowd continued talking, her eyes grew hawk-like, and Dean covered his ears, gesturing for Charlie to do the same. They knew what was coming next. Sure enough, same as the last year, Naomi snatched up the microphone, and let out a loud, blood-curdling scream. It echoed off the walls, and Dean feared for his hearing.   
Needless to say, the audience quieted down at once. Naomi once again regained her false smile, sickly sweetness spread across her face in a horrifying manner. Her bright red hair was pulled backward into a tight bun, an outer reflection of the orderliness that lurked inside. She began her long ramble about how if any students were to misbehave, then she and Zachariah would be in charge of their punishment personally. 

Dean rolled his eyes, nearly an annual occurrence at this point. This was his seventh time hearing this speech, and he didn’t care enough to pay it enough real attention. Seeing as it was still only Charlie’s second year, she had suddenly gone all pantsuit-and-seriousness and had all of herself focused on Naomi. 

He felt himself scanning the crowd, looking for any new meat on the faculty team. He had heard rumors of a new teacher, more specifically, a new art teacher, but he wasn’t entirely sure they hadn’t been just that; rumors. The more he picked over the staff, the more certain he became. Please, a new teacher? Zach and Naomi were too cheap. They’d rather cut the art program and split the profits. 

However, if he had bothered to look up at the stage again, he would have noticed the nervous man, practically shaking as Zachariah dragged him forward to where Naomi stood, microphone in hand. 

“Well, students, I want you all to give Mr. Novak a very warm welcome.” Naomi’s voice boomed throughout the room, and Dean’s eyes snapped upward. “He will be filling in for Mrs. Pamela, who is regrettably no longer with us.” The whole student body let out a shit ton of boos, for Mrs. Pamela was the favorite teacher of almost every student. Rumors were going around that she had gotten into a little pottery incident, causing her to lose her eyesight. 

“Quiet!” The room shushed immediately. “Now, as I was saying, Mr. Novak will now be replacing Mrs. Pamela as our school’s art teacher.”

Dean cast a bored glance toward the stage, quickly straightening up. A rather tall man, with dark, unkempt black hair, and startlingly blue eyes stood beside Naomi. A thin line of stubble covered his firm jawline. That man was attractive. Like, ridiculously so. It should have been illegal for any one guy to be that hot, Dean thought, any and all school-related ideas gone from his head. “Charlie.” He hissed, elbowing her in the stomach.

She shot him a dark look. “What the hell, Winchester? I thought we were friends.” She faked sobbed into her jacket sleeve.

“Is it just me or did the temperate go up a hundred degrees when Mr. McSexy came in? I mean, damn, that guy gives the one and only Dr. Sexy a run for his money.”

Charlie wacked him in the arm. “First off, we are at a school function. If the kids heard you swearing and calling another teacher ‘sexy’, I would have to find a new bestie. Naomi would fire your ass so fast, you would have to buy a new one. Second off, did you miss the whole conversation we had about me being a lesbian?” As she shook her head in mock shame, her curly red ponytail bobbed from behind her head. 

“Okay, so you’re a lesbian. Don’t mean you’re blind.”

“You got a point.” She gave the guy a quick once-over, lingering for a moment on the way that his shirt clung tightly to his chest, revealing a rather fit set of abs. No pudge there, unlike himself, Dean thought. “Alright, so I would climb that giant like a tree. Too bad I’m a lesbi-” She paused, holding her hand over her heart. “Hold on, wait a sec. Oops. Guess I’m bi now. Better get my grappling hook. It’s time to climb. I’m not kidding, Dean.” She said, her face serious.

“Who’s the inappropriate one now?” Dean asked, an eyebrow raised.

“Hey, come on. The kids aren’t even listening.” Charlie insisted, giving him a light slap to the belly.

“I was talking about how you so rudely tried to take away my Mr. Sexy, without even asking first.”

“Fine. Dean, do you mind if I take a ride on your new pony?” She wiggled her eyebrows suggestively.

“No way, Char-lay. That stallion is all mine.”

Just then, Dean felt a tiny hand grab his own. “Mr. Winchesta, Mr. Winchesta! Can I ride you pony?” Dean laughed, casting a glance at Charlie, who then left to round up her class. It seemed as though they had been so busy talking, they didn’t notice the assembly finishing. Or Naomi allowing classes to find their teachers. His students were sat on the floor, some crying, some talking, and some fighting. All except one little girl, who was clutching Dean’s hand like a safety raft. 

“Um, Bela, wasn’t it?” That morning, Dean had gone over everyone’s name, at least three times, but hardly any of them stuck. Well, a few did, such as Mary-Ellen and Bobby Winchester, his brother’s twins children. Also, Ben Braeden, the son of a past flame, named Lisa. That was a long time ago, though, 5 or 6 years. Before Dean realized just how much he liked guys, and how little he had interest in women. Anyway, the 5 year old in front of him bounced excitedly, twisting her curly brown hair around her finger. 

“Yes! My name is Bela Telbot and I am four and a half, but my mommy made them put me in here ‘cause I can already count to twenty and I know my alphabets. I love riding ponies! We have 7 at my house! I’m rich.”

Dean sighed. He loved kids, but then he met kids like this that made him question that. Kids that decided to show off and make his whole day difficult. “That’s great, kiddo. Wanna be the line leader?” Give her something to do. That’ll shut her up. When she nodded excitedly, he gently placed his hands on her shoulders, signaling for her to stay, while he gathered the rest of the line. 

“Alrighty, we got Lilith, Kevin, Ben, Mary-Ellen, Bobby, Hael, Raphael, Uriel, and Bela. I think that-” He stopped, casting a glance at his charts. “Wait. A-bad-don?” He looked up and down the line. “Abaddon? Hon?” The gym was nearly empty. “Crap. I already lost a kid.”


	2. My Hero

**Summary for the Chapter:**

> Dean meets Castiel, the hunky new art teacher. Meanwhile, Charlie runs into her one-night stand.

**Notes for the Chapter:**

> Thanks for all the kudos, bookmarks and comments I got on the last chapter! Feel free to leave more comments down below, positive or negative. Both are welcomed. :) I'm serious, reading comments helps me write faster and produce these chapters daily. No pressure, though. Thanks for reading!

Dean ran his fingers through his hair, while his class watched him anxiously. In seven years, Dean Winchester had never lost a kid. Ever. And now he had. “Stay right here, guys. Alright?” The class nodded and he raced around the auditorium, looking for that tiny redhead. He was so busy focusing on the kid, he forgot to pay attention where he was going, and ran straight into somebody.

“Hey! Watch it bud-” He stopped short, realizing who he had hit. Mr. McSexy himself. Novak.“Oh, uh, sorry man.”

“No problem. Look, there’s this kid in my office. She won’t leave. Any idea who I can return her to?” Novak looked stressed, as he ran a hand through his hair.

“Wait. Red hair, more pale than possibly natural?”

“Yes.” Novak looked extremely relieved. “She yours?”

“I may have lost her. I thought I was going to get my ass chewed out by Naomi. Thanks, man.” He stuck out his hand, “Name’s Dean Winchester.”

“Castiel Novak. Pleased to meet you.” The two men shook hands, and Dean finally got to get a good look at the guy. He was a tad shorter than himself, and god, those eyes. They were piercing blue, looking almost as if they were staring into his soul. 

“So, uh, Castiel. Hold on, can I call you Cas?”

“Well, I’ve never really had a decent nickname. My brothers’ Balthazar and Gabriel used to call me Cassie, but I prefer Cas.” Cas looked thoughtful, as though a nickname held the secret to the universe. Dean smiled. God, Novak was cuter up close. Way cuter.

“Anyway, Cas, about that kid.” Cas nodded, leading Dean to the doors of the gym. Dean told his class to follow him quietly, so that they weren’t disturbing other classes. They moved quickly, but had to practically go to the opposite end of the school to get to Novak’s office. Dean waited in the hallway with his class, while Cas grabbed Abaddon.

She practically skipped out of his room. “Hello, boys.” She gave a wave to some of the kids in her class, before pushing her way in front of Bela. Fortunately for her, Dean’s attention was back on Cas.

“My hero.” He said, in an airy, and surprising southern voice, clasping his heart.

Cas chuckled. “See you around, Dean.”

 

*

 

“Castiel!” A voice rang out from the end of the hall, and Charlie frowned. Where had she heard that voice before? “Castiel!”

Charlie followed the sound, slowly beginning to smile. “Anna?” She called out.

The second redhead spun around, sighing. “Crap.”

Charlie tilted her head, confused. She and Anna had had a lot of fun together the night before. Adult fun, as she and Dean so often put it. “What’re you doing here?”

Anna walked forward. “I’m looking for my brother.. He teaches here now. Castiel Novak?”

“Oh! Mr. Novak.. Yeah, I know where his class is. Walk and talk with me.” Seeing as the school day was finally over, the halls were empty, students all having left. Charlie let out a laugh. “I thought I recognized your voice. ‘Course last time I heard you screaming, it wasn’t your brother’s name.”

Anna blushed. “Look, Charlie, last night was great, and you seem like a great person. But, we can’t do that again. Ever.”

“What?” Charlie stopped, furrowing her brow. “Why not?”

“Because, we can’t be seen together. By my brothers or by anyone.” Anna raised an eyebrow. “Clear?”

“Wait a sec- Are you closeted?” When Anna nodded, however sheepishly, Charlie kept talking. “But, last night, you weren’t exactly all double-agent-Snape. You were pretty out there.”

“Yeah, well, it’s not going to happen again. My parents are religious freaks. If they found out about me, I would be disowned. Immediately. ‘Kay?”

Charlie had to admit, she felt bad for the girl. She had a body, and she knew how to use it. She just wasn’t allowed. And that sucked. For both her, and Charlie. “Alright.” Charlie shrugged. “But, when you do come out, I better be the first one you call.”

Anna rolled her eyes. “If I come out.”

“When you come out.” Charlie repeated, finally stopping at a small office. “Hold on a sec. I thought your name was Anna Milton.”

“Yeah, it is.” She nodded slowly.

“But your brother, is Castiel Novak.”

“Well, stepbrother. I kept my real dad’s last name.”

The first redhead nodded. “Of course. Look, I gotta go, but call me sometime? I know what you said, but think about it. You have my number.” The previous night, she had written it down on a napkin, kissing it with her lipstick before sending it Anna’s way. 

“Fine. See you, Charlie.” Anna gave her a smile, waving, before turning and going into Novak’s office. 

 

*

 

“See you tomorrow, Kevin!” The small Asian boy waved goodbye, his mother practically dragging him from the room.

“How was your day, loser?” Charlie waltzed into the room. 

“Kindergarten-y. Mind helping me get the paint out?” He gestured to his hair, his shirt, and his jeans. He was used to it by now, as was Charlie. She had to help him almost daily the previous year. The trials of being a teacher. 

“Ok, but first you will never believe what I just found out.” She was practically bouncing from excitement.

“What is it girl? Huh, huh?” Dean cried in mock excitement. 

With an eyeroll, Charlie continued. “Anna, that chick I banged last night, is the sister of, Mr. McSexy!” Dean shrugged, leaning against his desk. “Why aren’t you more excited? We can go on double dates now!

“Cas and I are strictly professional.” Dean crackled a smile.

“Uh huh, you and Cas. Professional.” Charlie laughed disbelievingly.

“Whatever. Shut up and help me get this paint out. They’re waiting for us at the Roadhouse.”


	3. Run-In at the Roadhouse

**Summary for the Chapter:**

> Dean and Charlie head to the Roadhouse for dinner, and end up getting served the surprise of a lifetime. New information about Dean's past comes to light.

**Notes for the Chapter:**

> Sorry I didn't get this posted sooner. I have mono and was in the hospital for a couple days. I'm super tired and kind of hurried, so this probably might not get posted until tomorrow, or it might be kind of eh. Anyway, have fun reading, thanks for the comments, kudos, and bookmarks. I really love seeing them. Feel free to leave comments, it might take a little while, but I will read and answer them. Anyway, enjoy, my lovelies.

If there was one thing that Dean loved about Kansas, it was the Roadhouse. It's creaky doors, old battered, wooden counters, and friendly faces. Over the past 13 years, Dean had come to call this place home. After all, where else would home be? Dean had known many tragedies in his life, many lies, many deaths, and so much pain. But, despite all that, he had ended up here, which had to mean something, didn't it? 

When Dean was about 6, his home was burned down, his mother, Mary, taken from him forever. It left a larger hole in Dean's heart than he thought humanly possible. He had missed his mother, more than anything, but his father lost his mind after her death. He became convinced that a monster had murdered his wife, a yellow-eyed demon, as he most often called it. Of course, that wasn't true. 

Later that night, a young man was caught. His name was Azazel, and apparently, he was quite drunk. Young, drunk Azazel had been offended by Dean's father, John, earlier that week. John had called him dirty, poor and a thief, after he came into John's auto-shop. So, in order to get revenge, he had set fire to the Winchesters' home, killing his wife, and nearly stealing the life of the youngest Winchester. Fortunately, Sammy had been rescued, and his life remained intact. Sadly, the same could not be said about Mary Winchester. 

John Winchester, driven mad with pain, had took his two sons cross-country, looking for the demon that killed his wife. However, seeing as that demon didn't exist, he spent years tracking nothing. Over the years, he became angry at the lack of results, and took it out on his sons. Dean took most of the beatings, always the protector of his smaller brother. In the end, John had 'summoned' the demon, and a young teenager happened to be in the wrong place in the wrong time. 

The Winchesters were the cause of 15 year old, Ava Wilson's death. Afterward, unable to live with his father's actions, Dean called the police, and John was taken away. It seemed like the end of Sam and Dean's pain. 

After his father was locked up, leaving his sons as orphans, an old family friend and his wife had taken them in. Bobby Singer, and his fiery sweetheart, Ellen Harvelle, who was too dignified to take Bobby's last name. The older couple had two children, one daughter, and one son. Joanna Beth Harvelle was the first child they had, born 6 years after Dean. A few years later, Ellen got into a car accident, ruining any chance they had of another child. They were devastated. 

It was only a year later, when they decided to adopt a son. Garth Fitzgerald IV, who wanted to keep his own last name as a salute to his heritage, became the newest edition to their family. Ellen and Bobby led a happy life, thanks to their children, but soon, they were thrown the curve-ball of a lifetime. Once Bobby's best friend, John Winchester was in jail, facing life there together, leaving two pained children in his wake. 

At first, Bobby hadn't wanted to take in the boys. He hadn't seen them since they were babies, and knowing what his father had did to them in those years, knowing that John had taught them to shoot guns, throw knives, and kill someone with their bare hands, it seemed like more trouble than they were worth. Of course, Ellen had talked him into it, saying how it was the right thing, and they had room for two more. 

It seemed that Dean and Sam were always going to be in her debt, seeing as she had changed their lives. And on occasion, when Dean or Sam would complain about chores, and an extra trip to the grocery store, she would nonchalantly shrug, mentioning how they would be on the streets if it wasn't for her. She wasn't serious, holding it over their heads, but it got the work done, and they kept on being on a family. 

The only people who knew about Sam and Dean's secret was their little family. Sam, Dean, Bobby, Ellen, Jo, and Garth. Dean hadn't even had the guts to tell Charlie. He knew, deep down, if Charlie found out, she would leave him. Faster than a blink of an eye. After all, why would she stay? He was a murderer. So, Dean kept his secret, not telling a soul. But, keeping a secret has certain catches. He had to hide the real reason he lived with the Singer-Harvelles. He had nightmares about the girl's death. Her screams and pleas for her life. Most of all, it was the fear. The constant, unrelenting fear, which was more reliable than anything else in his life. The constant fear that someone would find out his secret, that someone would rip apart the life he had led so carefully. 

 

*

 

"Heya, Ellen." He leaned over, giving the aged woman the kiss on the cheek. "Where's Bobby?"

Ellen rolled her eyes. "Where else, boy? Working on those damn cars." Her tone was happy, yet tired. "Mind popping out and grabbing him for me? Soon as he gets over here, we can get some grub. Burgers, as usual?" She grinned, he always loved her burgers.

Dinner at the Roadhouse was a tradition with their family. Every Sunday night, and on special occasions, such as the first day back at school. He usually brought Charlie along, and Sam always had Jess and the kids in tow. Nobody dared to miss Sunday dinner, or they would face Ellen's wrath. Besides, when you had a family like this, you never wanted to miss it. 

Dean smiled. "Sure thing, Ellen. Charlie's grabbing her jacket and she'll be right in." He gave her a small hug. "Be right back."

He heard the door swing open, and assuming it was Charlie, he ignored it, disappearing out the backdoor to grab Bobby. 

As usual, Bobby was leaned over a car, grease covering the edges of his face. Dean laughed to himself as he heard Bobby cursing at the car. "Run, you damned thing." He murmured. 

"Hey, Bobby!" Dean called, sending Bobby jumping at the sound of his voice. 

"Bout time you showed up." He slammed the hood of the car, walking over to where Dean stood. "You're late."

Dean shrugged. "A few minutes, that's all. At least I'm clean."

The older man narrowed his eyes. "Watch it, boy." With a playful smack on the arm, he headed back inside, Dean on his heels.

Charlie was waiting by the backdoor, eyes wide. "You are never going to believe this, man."

"What?" Dean asked, amused. 

"Mr. Sexy is here. And he brought guests." Dean pushed his way past her, wanting a better look. Mr. Sexy- er, Cas- and seven other people entered the Roadhouse. At the front, two tall men, handsome twins. Then, following closely, a shorter, pudgier man, his hair a golden blonde. He face was lit up in a grin. Behind him were two redheads, immediately, Dean recognized one as Naomi. Why was she here with Cas? The other redhead was prettier, but cast her eyes over the bar in a disapproving glance. Lurking by the door were Cas, and a taller, blonde guy. The two were deep into conversation, despite the fact that a short, pretty brunette was waiting with her hand on Cas' hip.

Dean felt a surge of jealousy. Who was this? Ellen was on her way to seat them at a table, when Dean grabbed her arm. "I got this one."

She gave him a suspicious look. "You know them?"

"Well, one of them." His eyes fixed on Cas, who was now looking at the brunette, adoration in his eyes. 

"Alright, hon. I'll start on dinner." She turned, heading back to the kitchen. 

Dean started back towards the large group, and he felt an urgent hand on his shoulder. "What are you doing?" Charlie hissed. 

"Stuff. Now, remove your hand or I will break it." Charlie rolled her eyes.

"Like you would even know how." Oh Charlie. If only you knew.

"Whatever. I'm gonna go help out my elderly mother by seating a table."

"Oi! I heard that!" Ellen yelled from somewhere behind them. Dean grinned as Charlie dropped her hand. 

"Then I'm helping. Anna's over there. I want a chance to talk to her." She nodded her head at the second redhead, beside Naomi. 

"If you can keep up with me." The duo walked over to the crowd, Dean suddenly all business. "How many?"

One of the twins, smirked rudely. "Eight, nimwad. Can't you count?"

"Nope. But I can spit in rude customer's food." 

The twin rolled his eyes. "Just get us a table."

Dean glanced at Charlie, and they led them to the second biggest table in the joint, on the opposite end of where the Singer-Harvelle-Other family usually resided.

That was when Cas finally looked up, his eyes landing on Dean. "Hello Dean." He said, surprise in his voice. "Do you work here?"

"Nah. My mom, er-Ellen, owns the place. I'm helping her out." While the rest of the group sat, Cas wandered over to Dean. "I gotta say, you have a weird choice of friends."

"This is actually my family, Dean." He looked at the curly-haired female. "And my girlfriend, Meg." She blushed. 

"Um, nice to meet you, Meg."

"Same to you, Dan." Dean frowned. Now she had done that on purpose. 

"It's Dean." He corrected her, trying to keep the condescendingness out of his voice. He didn't like this girl, already.

Cas seemed to be aware of this, and went on with introductions hastily. "Um, the twins are Michael and Lucifer. The one with the scar by his ear is Lucifer. Next is Gabriel," he said, motioning to the short, blonde guy, with the big smile. "You know Naomi. This is my other step-sister, Anna Milton. They are fraternal twins. The blonde guy by them is Balthazar."

Dean nodded, still trying to get over the fact that Naomi was related to Cas. Mr. Sexy. Ugh. About that time, the door swung open and Sammy, Jess, little Mary-Ellen and Bobby entered. "That's my little bro, Sammy and his wife, Jess. That's their kids; Mary-Ellen, and Bobby." While Jess and the kids sat down at their table, Sam wandered over, and as per usual, towered over his brother. 

"Hey, Dean. Who's this?" He looked over at the raven-haired man, curious. 

"This is Cas. He's the school's new art teacher."

Sam nodded, running his eyes over the table. Suddenly, he stopped, mouth slightly agape. "Gabriel?"

"How did you-"

He barely got to finish his sentence as Gabriel jumped up, and grabbed Sam in a bone-crushing hug. The two broke apart quickly, Sam looking scandalized. "Heya, Sasquatch." Gabriel said with an amused grin. 

"Gabriel, you know Jess." He gestured to the table a few feet away. "She's my wife now. And those are my kids." He said slowly, the blush slowly fading from his cheeks. 

Gabriel slowly nodded, embarrassed. "Sorry, Samalam. Didn't know." He returned to his seat, his smile gone. 

Castiel and Dean shared a long look, and Dean led Sam away. "Charlie, get their orders, eh?" He murmured, before leaving.

"Who was that?" Dean asked, as soon as they were out of earshot of the table.

"Gabriel. You know, the one I dated in college." Sam looked embarrassed, and he shifted awkwardly. "We broke it off after a couple weeks, when I met Jess. No big deal."

"You sure?" Dean raised an eyebrow. Sam had mentioned Gabriel, when they first started going out. Swearing that they were 'meant to be' and all that jazz. When he had met Jess, and they started hanging out, she was the cause of a lot of fights in their relationship. Driven by jealousy, Gabriel had broken it off, and Sam was in mourning for months. Then, Jess and Sam started going out, and he got over his 'first love'. 

"I'm fine, Dean. Need I mention my wife and kids are waiting for me?" Sam pulled bitchface #37 and punched him in the arm. 

"Whatever you say, bitch."

"Jerk." Sam rolled his eyes, sliding into a seat by his wife. Despite the fact that he had a wife, two kids, and three dogs waiting at home, Sam kept sneaking glances at Gabriel. If they hadn't broken up, maybe Gabriel would be seated beside him now. Maybe these would be his kids. Maybe that would be their home. No. 'Stop it, Sam.' He thought forcefully. 'You're married. Gabriel probably has somebody else. He's moved on. So have you.' So, with another forlorn look at Gabriel, he gave his wife a kiss on the cheek, and plastered a smile to his face. Yes. He was over Gabriel. Or was he?


	4. Shut Up and Chow Down

**Summary for the Chapter:**

> The Singer-Harvelle and Co. family enjoy a good old fashioned meal, complete with lots of jealous pining.

**Notes for the Chapter:**

> I'm really sorry that it has taken so long to update. I've had severe writer's block, and just haven't really felt up to writing. I just want to say thank you all so much. I legitimately cannot believe how many hits, kudos, and bookmarks this has gotten. I am so incredibly happy that you guys are enjoying this as much as you are. I appreciate all of your support, more than I can express! Anyways, thank you for reading! Feel free to leave more comments, I respond to them all. Also, kudos and bookmarks are loved and cherished. Okay, well, go on and read now!

Dean Winchester was  _not_ a jealous person. He just didn't get jealous. Simple as that. He never really had a reason to be. He never really had a boyfriend, or girlfriend, nor did he develop crushes. So, overall, Dean Winchester didn't have anyone to get jealous over. And that wouldn't change now. Not over some guy, however stupidly attractive he may be, with his stupid messy dark hair, and his stupid blue eyes. No. Dean wasn't jealous. Not at all. He wasn't jealous when Cas had his arm draped across Meg's shoulder. He wasn't jealous when he and Meg kissed. Nope. Not jealous at all.  

"Dean?" Ellen's voice called out, pulling Dean from his thoughts. 

"Huh?" His eyes widened, everyone watching him. Charlie snickered into her sleeve, as Dean's face grew more and more red. 

"Bobby and I were wondering how was your first day back teaching. Got any favorite students yet?" She popped another fry into her mouth, the corner of her lips turning up in a smile. 

"He certainly has a favorite teacher." Charlie mumbled, nudging him in the ribcage. Dean shot her a dark look, swallowing his mouthful of burger. 

"Nah. I mean, they're cute kids. They're sweet." He nodded slowly, suddenly desperate not to have the attention on himself. "What about you, Jo? How's your first day back at class?" Jo had a part-time job teaching martial arts at a studio near the elementary school. When she wasn't working there, she spent her time picking up shifts at the Roadhouse, and helping out Ellen. 

Jo gave him a suspicious look, but shrugged. "It was fine, I guess. Rufus said to tell you 'hi' by the way, Dad."

"How is Rufus these days?" Rufus and Bobby had been hunting buddies when they were younger, but after Bobby had met Ellen and started his own family, the two grew apart. Now, Rufus owned the martial arts studio, and was Jo's boss. 

"He's fine. Rumor is he's planning on selling the studio, though." 

"That sucks." Garth chimed in from the end of the table. 

"No joke. I love working there."

"I can go down there and talk to him if you want," Bobby suggested. 

"Thanks, Dad." She smiled, turning back to her burger. There was silence for a few minutes, as everyone ate, when Garth spoke up. 

"Nah, it's fine. Don't bother asking me how my day went." He said, in a mocked hurt tone. Dean laughed, knowing Garth was only kidding. 

"Fine. Hon, how was your day?" Ellen rolled her eyes, kindly smiling at her adopted son.

"It just so happens, I got a promotion. And, I met somebody." Garth worked for the local police station, one of the city's finest cops. 

"Oh, really?" Ellen's asked excitedly. 

"Yeah, she's great. Her name's Bess. Her dad is the reverend at the church." He blushed. "We have a date tomorrow night."

"That's awesome, Garth." Sam chimed in. 

Dean found himself zoning out of the conversation, paying more attention to the Novak table than his own. The twins seemed to be fighting with each other, while Gabriel was trying (and failing) to calm them down. 

"Hey, um, Dean? Can I see you for a minute in the back?" Charlie asked, tugging him out of his seat. He followed, albeit reluctantly.

"What?" He practically snapped. 

"You need to keep it in your pants, okay? You've been staring at Novak for the past five minutes. You're practically freaking drooling."

"Sorry." He frowned. "Was it that obvious?"

"What do you think?" She retorted, eyebrows raised. 

"Whatever." He shook his head. No big deal. The two returned to the table, and Dean spent most of the rest of the time in silence. Eventually, he realized that he had left his phone in his car, and he excused himself from the table. 

He was digging around in the front seat of the car when he felt a tap on his shoulder. He jumped, turning around. Meg, Castiel's girlfriend, stood there. "Got a lighter?" She lifted her cigarette. 

"No," he lied, knowing full well that he always carried around a lighter. 

"You don't like me, do you?" She commented, raising an eyebrow. With her neck tilted back, you could see more of the tattoos poking out of the collar of her jacket. 

"Why'd you say that?"

"Because you have a lighter poking out of the pocket of your jacket." She used her cigarette-free hand to gesture to it. "And you've been shooting me death glares for the past half hour."

"Oh, that was you?" He responded, a joking tone to his voice. 

"Haha. So funny, Winchester." She rolled her eyes. "What's your problem with me?"

"Don't have one. And, uh, I have to go." He slid past her, closing the door to the impala behind me. "See you around, Martha."

"Meg," she corrected him, her brown hair swinging over her shoulder. 

"Yeah, see ya." Dean started to walk back towards the restaurant, vaguely aware of Meg following him. She was barely back at her table, already pulling Castiel in for a kiss. 

_That bitch._ Dean thought, feeling a familiar tug of jealously in the pit of his stomach. _This isn't over._

**Notes for the Chapter:**

> I'm sorry this chapter wasn't the best, and it was so short, but I am hoping that once I establish a good beginning with the story, I can move on and get to the better chapters. :)


	5. Sweet Dreams

**Summary for the Chapter:**

> Dean's dreams are filled with the memories of the past.

**Notes for the Chapter:**

> I've been really uninspired lately, but I hope this chapter will make up for it. I love you all, and I really appreciate your support. :)

_"Do it, Dean. Now. Do it." The voice urged Dean forward, his mind racing. "Hold it still." His eyes lifted, landing on his father's angry, unforgiving expression. John's long callused fingers traced over the handle of the knife. They stood in an old wooden shack, the walls nearly collapsed. In the center of the room was a small chair, and sat on top of it was a girl, no more than 15._

_John Winchester was convinced that the young girl had killed his wife. Why, Dean didn't know. And now, Dean's father was going to kill her, and he expected Dean to help. Dean, who was only 14. Dean, who was terrified. Dean, who had never wanted to hurt anyone. But that didn't matter; not to John. "She killed your mother. It's her or Sam!" His father barked._

_Dean stumbled towards the weeping girl, her hair matted around her face, her eyes pleading. "Please. I-I don't know anything about your mother."_

_He turned his face towards his father. "I-I don't think she did it, Dad, please."_

_"Dean. It is lying. It is a monster, a demon. Now. Hold_  it  _down." John commanded. Dean obeyed, gripping her arms tightly to the chair where she sat. Her screams filled the air as his father plunged his knife into her flesh, it tearing and ripping. Tears streaked down his ashen face, wishing he were anywhere but here. He wanted to run, leave everything and get as far away from his father as he could. But he couldn't. He had to protect Sammy. No matter the cost._

 

*

 

Dean snapped awake, sweat dripping from his face. It had been so long, so many years, yet he still had the nightmares. Memories of what he had done seeped into his dreams, ruining another night's rest. When would it end? But then again, he didn't deserve to be free of the dreams. He could have-no,  _should have,_ stopped his father. But he didn't. He held down that poor girl and watched as his father ended her life. She was dead, and like it or not, it was his own fault. 

With a groan, Dean pushed himself up, forcing himself to get ready. He had to go to school, mold the minds of the future generation, and all that. He left his room, heading down the short hallway and knocked on the door to Charlie's bedroom. The two had been sharing the apartment for almost three years now. 

"Morning," he called through the door. 

"Mmhmm.." Charlie mumbled. 

"Up and at em!" 

"Yeah, yeah, ten more minutes." She groaned, and Dean heard the distinct sound of her burying her head into her pillow. 

"I'm going to give you ten more seconds before I come in there and drag your geeky ass out of bed." 

"Oh yeah, I'm the only geek here." Despite her aggravated tone, the springs in her bed groaned as she got up. "Happy?" She snapped a moment later, the door opening.

"Ecstatic." He turned, heading into the kitchen to make breakfast.  

 

*

 

Dean's day had been rather uneventful. He and his students had started going over the alphabet, and Bela had been perfectly giddy to point out that she knew it already. She had been even more happy to rub it in the other children's faces. Dean was having a hard time trying to explain why she shouldn't do that, seeing as she wouldn't stop talking for two seconds so that he could. 

At lunch, things had started to turn around, as he finally got to see some friendly faces. At Kansas Elementary, lunch monitors (usually parent volunteers) would watch over each class, and the teachers sat together. Dean quite liked that system. Every day, Dean sat with the same teachers. Charlie, and Benny, another kindergarten teacher who Dean had become quite fond of. 

Benny was handsome, no point in lying there, not to mention how nice he was, and how great a chef. This particular Tuesday, Benny had brought in a tupperware container of his world-famous grits, for each of them, as well as a small box of brownies.

"Benny, I think I love you." Charlie said dramatically, taking a large spoonful of grits. "Nope. I know I love you."

"Well, if you say so." He blushed, stirring his own grits. "What do you think, Dean?"

"Uh, I mean, I guess you two'd make a cute couple." He shrugged, grinning.

"No.. About the grits."

"Benny, I was the one who demanded you make me some. And I guess it'll have to do, seeing as you didn't make any pie."

"There are other foods than pie."

Dean frowned. "That has yet to be proven."

Benny rolled his eyes. "How about this? You come over tonight around 6, and help me with my website, and I'll make you all the pie you want." Benny had wanted to open his own pastry shop forever, but he didn't quite have the money yet. For now, he was operating from his own kitchen, making cupcakes, pies, cakes, and other pastries whenever he had time. 

"Sounds like a plan." Dean replied, finishing off his bowl. 

Benny nodded, then sighed, staring beyond their table. "Crap. One of my kids is vomiting. I gotta go handle that." He jumped up, smiling apologetically. 

The moment he was gone, Charlie smacked his arm excitedly. "I can't believe this!"

"I can. The cafeteria food here could make anyone sick."

"No.. I mean, you.. And Benny!"

"I don't follow.." He raised an eyebrow. 

"You have a date tonight." She said, as though it were the most obvious thing it the world. 

"Nah. He's just making some pie while I help him out. Ya know.. Like friends do."

"Nope. He totally just asked you out!! And you accepted."

"Wait.. Really?" 

"Yes!" She exclaimed. "I knew that Benny was into you.. Like, right from the beginning.. But I didn't know you liked him too."

Dean frowned. He hadn't really thought of Benny that way. But, Benny was nice. He was attractive. He was good for Dean, right? "So, you're like 100% sure that it's gonna be a date?"

"Yes!" Her eyes were practically bugging out of her head. Dean couldn't help but smile. 

 

*

 

It was only a few minutes before six when Dean found himself standing outside of Benny's apartment, wearing a dark green Henley under his leather jacket, as well as his best jeans. He knocked lightly, and before he knew it, he was standing face-to-face with Benny.

"Come on in," Benny stepped aside, allowing Dean entrance. 

"Thanks." He muttered, sliding it clumsily. 

"The pie's in the oven. I'm gonna pull up the website. There's this bug and some people are having trouble ordering." Benny slid over to the kitchen counter, logging into his computer. 

"Yeah, I'll have a look." To be honest, he didn't have a clue about all this tech stuff. That was Charlie's area of expertise, but he wasn't going to object to helping him out. The two men sat in silence for a few minutes, as Dean looked over the website, checking anything and everything he could think of. Unfortunately, nothing worked. "Hey, I'm sorry, man." He apologized, sitting back. 

"It's fine," Benny rubbed a hand down his chin, covered in a thin layer of scruff. "Pie's probably done." He hustled over to the oven, unloading the pie, which appeared to be apple, and bringing Dean and himself a piece. 

"Benny.. You've really outdone yourself." He plopped a second, even larger bite in his mouth, stopping to savor it. "This. Is. Fantastic."

Benny's light blue eyes seemed to light up. "You mean it?"

"Absolutely!" Dean smiled. He laughed, reaching over and wiping a stray crumb from the corner of Benny's lip. He had done it before he even realized what he was doing. "Uh, sorry about that." He dropped his eyes, mildly embarrassed. 

"Not a problem," came a soft reply. Dean looked up once more, and before he could help himself, he was kissing Benny. What had started out as soft and gentle, quickly became rough as Benny's hand slid down Dean's chest, reaching around his waist and pulling him closer. They were a cluster of hands and limbs, pulling, tugging, grasping at hair, clothing, anything to pull each other closer, to close the distance between one another. 

"Bedroom?" Benny's rough voice suggested. Dean barely nodded before he felt himself tugged away. His night was looking up. 

**Notes for the Chapter:**

> Yeah, I don't know what happened. It kind of got away from me there.


End file.
